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Vacation rentals with a pool in Highland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Highland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A private pool area features a natural stone water slide, surrounded by lush greenery and palm trees. A hot tub is positioned beside the pool, with colorful flowers in a planter nearby. Vibrant patio furniture adds a touch of comfort to the outdoor setting.
Villa in Rancho Cucamonga
4.87 out of 5 average rating, 137 reviews

Gorgeous Resort Style Mountain view Pool Villa

Gorgeous 3 bed/2 bath single floor home with PRIVATE Heated POOL that feels like a 5 Star resort with FREE EV charging for your car. Beautiful backyard, BBQ grill and 12 seater lounge, pool & hot tub with water slide. Fireplace, 85” OLED TV, work space, High speed Wi-Fi , Gym. Fully equipped kitchen, 6-burner gas range stove, rice cooker, coffeemaker etc. Laundry room with washer/dryer, iron/board, air conditioning, heating, linens/towels, Pack & play. Digital door lock, Driveway for 4 vehicles.

Guest favorite
A cozy living area is displayed with a stone fireplace, flickering with flames. A circular wooden coffee table, featuring a plant in a terracotta pot, is positioned in front. Brown and beige decor elements add warmth to the space, complemented by patterned wall art.
Condo in Big Bear Lake
4.87 out of 5 average rating, 374 reviews

Lakeside Condo 2B/2B - Jacuzzi, 3mi to slopes

Enjoy a Santa Fe vibe with hand painted murals and other unique interior details. Play with dimmable lights to create the perfect mood. Gather by the spacious kitchen countertop. Sit by the wood burning fireplace or relax on the balcony facing the pool. Enjoy the heated spa or walk 100 yards to the picturesque Boulder Bay to fish, swim, rent a kayak or a paddle board. The popular Castle Rock trail is a walking distance away. Big Bear Village is only 2miles away and it is 4 miles to the slopes.

Superhost
A dining area is visible with a wooden table surrounded by four chairs, positioned against a green accent wall. Near the table, a television is mounted on a light-colored wall unit that features decorative items and small plants, enhancing the welcoming ambience of the space.
Condo in Downtown Riverside
4.88 out of 5 average rating, 229 reviews

Quaint Farmhouse Getaway - Entire Place (Condo)

Enjoy your stay at this farmhouse style 2 bed 2 bath condo! Extremely clean and well maintained, this space is conveniently located a few minutes from the downtown area, Central Plaza, and walking distance from Riverside's well known Mt. Rubidoux Hike; a 1-mile trek that gives a stunning view of the entire city. There is a park across the street that kids love which also has a nice walking path. The neighborhood is very quiet and peaceful. Access to Wifi, washer/dryer, 2 car garage, and more!

Guest favorite
An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.
Home in Cherry Valley
4.89 out of 5 average rating, 108 reviews

Vineyard Retreat, Pool & Amazing Views!

Experience luxury in this 6-bedroom vineyard estate with a grand pool, hot tub, and breathtaking views. Perfect for family gatherings or quiet retreats, our home offers a wheelchair accessible King suite, a music room with a grand piano, a dining area and billiards. Minutes from Serendipity Garden and historic Yucaipa Uptown, this property also features a full kitchen, outdoor BBQ and a full living room with 80" TV. Event chairs and tables available—ideal for celebrations or serene getaways!

Top guest favorite
The outdoor space features a sparkling swimming pool surrounded by a landscaped patio. The cottage is seen in the background with large glass doors, inviting natural light. Beautiful plants and greenery enhance the serene atmosphere, providing a pleasant space for relaxation.
Guesthouse in Redlands
4.99 out of 5 average rating, 334 reviews

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

Guest favorite
A spacious living room features high cathedral ceilings and large windows allowing natural light to enter. Modern blue sofas are arranged around a glass coffee table, complemented by stylish accent chairs. A lush indoor plant adds a touch of greenery, enhancing the warm atmosphere.
Villa in Redlands
4.92 out of 5 average rating, 154 reviews

Peaceful Private Retreat In The Heart Of Town

Meticulously designer-renovated modern home “The Nest “is surrounded by mature tree and nestled beneath the mountains in South Redlands. Whether you’re looking to spend time with loved ones, vacationing or work remotely in a peaceful environment, this is the place to do it all. Relax by the fireplace while light pours in from the wall of windows, with pleasant sparkling pool, grill and chill on the backyard, and explore nature right outside your front door. Conveniently located in Redlands!

Top guest favorite
A two-story mini home is showcased beside a refreshing swimming pool, surrounded by a neatly landscaped garden filled with various plants. The clear blue sky enhances the peaceful outdoor atmosphere, while a palm tree rises above the structure.
Guesthouse in Fontana
4.95 out of 5 average rating, 241 reviews

The Blue Cabin

Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. No parties allowed.(SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

Guest favorite
A serene backyard pool area is showcased, featuring clear blue water and colorful pool floats. Lounge chairs are arranged along the poolside, with a privacy fence visible in the background. Palm trees add a tropical touch to the inviting atmosphere.
Home in Riverside
4.92 out of 5 average rating, 154 reviews

Cozy Getaway 3BR House + POOL+BBQ PATIO+Games!

Enjoy the sunny California Dreamin’ lifestyle in our beautiful 3 bedroom, 2 bathroom spacious home! Take in the SoCal vibe by lounging in our private backyard pool and use our outdoor kitchen's BBQ grill and patio dining area. The large living room and full kitchen make it easy to relax and entertain. Located in a serene neighborhood surrounded by desert hills, Downtown Riverside is still only 8 minutes away! Unwind, decompress, and enjoy creating new memories in this DREAM home!

Guest favorite
An outdoor space is presented, featuring a sparkling pool and a relaxing Jacuzzi under a wooden gazebo. Colorful murals adorn the surrounding wall, with warm light illuminating the area at dusk. Comfortable lounge chairs are positioned around the pool for leisure.
Home in Wildwood Park
4.81 out of 5 average rating, 214 reviews

Hot Tub, Fire Pit/Game Room/ Near NOS Center

Welcome to our meticulously clean three-bedroom, two-bath haven in San Bernardino! This gorgeous house is designed for comfort and entertainment. Unwind in the game room with a pool table or gather around the patio's fire pit. Experience the charm of our outdoor space, featuring a second fire pit in the grass area. Create lasting memories surrounded by freshly painted murals near the inviting pool and brand-new Jacuzzi – perfect for starlit evenings with friends and family.

Guest favorite
A comfortable living area features a brown sofa and two green chairs arranged around a circular black table. Light streams through sheer curtains, enhancing the warmth from a fireplace. Decorative plants and a subtle lamp complete the inviting space.
Condo in Big Bear Lake
4.94 out of 5 average rating, 183 reviews

Casita Condo | Jacuzzi | 3mi to slopes

Completely renovated with a unique style and trendy touches, the Casita Condo features Spanish accents throughout the home, with arches and terra-cotta details. Enjoy the brand new kitchen, with all upgraded appliances, including a wine fridge. Gather around the fireplace and Smart TV where you can access all your favorite streaming services. The two bed/two bath layout is ideal for small families or two couples looking to enjoy a mountain getaway.

Guest favorite
Home in Grand Terrace
4.91 out of 5 average rating, 160 reviews

Riverside Serenity Winter Oasis|Spa/Pool/Mini Golf

Welcome to our exquisite Riverside retreat, where luxury meets family fun! Here's what makes our place truly special: 🔥 Cozy Fireplace for Chilly Evenings 🌴 Tropical Oasis with a Sparkling Pool 🌟 Jacuzzi Bliss under the Stars ⛳ Mini Golf Extravaganza. 🏡 Spacious and Clean Rooms 📍 Centrally Located Convenience: Downtown Riverside, UCR, NOS Center, 210 Freeway, Yaamava, and local shops *~Fun-Filled Family Environment!~* Book now!

Top guest favorite
Guesthouse in Highland
4.93 out of 5 average rating, 165 reviews

Dreamy Escape Private Entrance /pool/near Yaamava

Our location is close to dining, hiking, shopping, movie theaters, and popular attractions like the National Orange Show Event Center (NOS), Yaamava Resort & Casino, vibrant nightlife, Redlands University, and Loma Linda University. You'll love our place for its location, inviting ambiance, outdoor space, and friendly neighborhood. It's the perfect spot for couples, solo adventurers, and business travelers looking for a cozy getaway!

Popular amenities for Highland rentals with a pool

When is the best time to visit Highland?

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Avg. price€ 76€ 90€ 91€ 102€ 91€ 102€ 96€ 94€ 93€ 95€ 91€ 79
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Quick stats about vacation rentals with a pool in Highland

  • Total vacation rentals

    Explore 20 vacation rentals in Highland

  • Nightly prices starting at

    Highland vacation rentals start at € 35 per night before taxes and fees

  • Verified guest reviews

    Over 1,320 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Highland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Highland rentals

  • 4.9 Average rating

    Highland stays are highly rated by guests—averaging 4.9 out of 5!